Production of acridinium compounds



Patented Mar. 16, 1926.

UNITED STATES PATENT OFFICE.

LOUIS BENDA, OF MAINKUR, FRANKFOBT-ON-THE-MAIN, AND OTTO SIEVERS, OFFECHENHEIM-ON-THE-MAIN, GERMANY, ASSIGNORS TO LEOPOLD CASSELLA. & CO.GrESIEILIIYJSCHAIET MIT BESOHRANKTER HAFTUNG, A CORPORATION OF GER-MANY.

PRODUCTION OF ACRIlJINI'UM COMPOUNDS.

No Drawing. Original application filed December 22, 1923,Seria1 No.682,305. Divided and this application filed April 18, 1925. Serial No.24,272.

To all whom it may concern:

Be it known that we, LoUIs BENDA, a citizen of the;Swiss Confederation,residing at Mainkur, near Frankfort-on-the-Main, Germany, and O'r'roSIEV'ERS, a citizen of the German Empire, residing atFechenheim-on-the-Main, Germany, have invented certain new and usefulImprovements in the Production of Acridininm Compounds, of which thefollowing is a full description.

This application is a division of a previous application of the abovenamed inventors, filed December 22, 1923, Serial No. 682,305.

We have found thathydroxyacridines, as for instance,3.6-dihydroxyacridine (Benda, B. Ber, 45, 1704:), may be alkylated inthe acr'idin'e nitrogen, without being at the same time alkylated in thehydroxyl group, if alkylation is carried out in the absence of acidbinding agents.

According to this invention therefore new acridiniu'm compounds areproduced by alkylating a hydroxyacridine in the acri dine nitrogen.

In consequence of their high bactericidal property and low toxicity, thenew acridinium compounds are excellent antiseptics; their character asdyestuffs is hardly apparent and so they contrast favorably with thecorresponding amino-acridinium compounds. They are more soluble and havegreater power of diffusion than the salts of 3.6-dimethoxyacridine,3.6-diethoxyacridine, 3.6-dihydroxyethylacridine and other compounds ofthe application No. 634,895 of April 26, 1923.

Example. 3.6-dihydrowyJO-mcthgMWMdwnchloride,

80 litres nitrobenzene are heated to 180.

liquor is decanted by suction. The mass, after being washed with ether,is boiled for some length of time with the addition of 5 litreshydrochloric-acid and 200 litres water until the toluenesulphonicacidcompound has been transformed into the methyl chloride, then filteredhot and the latter precipitated with hydrochloric acid or common salt.By again dissolving in water and precipitating, the compound is obtainedas yellow needles, which very easily dissolve in caustic soda solution.

, From the alkylating filtrate further quantitles of the product may beobtained.

Instead of the p-toluene sulfonic acid methylester other esters andother alkylating agents, such as methylor ethyl chloride or-iodide etc.may be applied.

Having now particularly described and ascertained the matter of our saidinvention and in what manner the same is to be performed, we declarethat what we claim is:

1. A process for the production of hydroxyacridinium compounds byheating hy droxyacridines with alkylating .agents in the absence ofacid-binding agents.

2. A process for the production of 3.6 10-alkylacridinium salts byheatdihydrox ing 3.6 ihydroxyacridine with alkylating agents in theabsence of acid-binding agents.

3. As new substances hydroxy-lO-alkylacridinium-compounds.

4. As new substances 3.6 dihydro'xy-lO- ,alkylacridinium-com ounds theconstitution of which correspon s to the formula.

v ,bn

. no on x in which formula R means an alkyl radical and X means ananion, being yellow needles,-

which very easily dissolve in caustic soda solution.

In witness whereof we have hereunto signed our names this 19th day ofMarch,

1925. LOUIS BENDA. OTTO snavnns.

